Literature DB >> 20820680

Chiral BINOL-derived phosphoric acids: privileged Brønsted acid organocatalysts for C-C bond formation reactions.

Alexandru Zamfir1, Sebastian Schenker, Matthias Freund, Svetlana B Tsogoeva.   

Abstract

BINOL-derived phosphoric acids have emerged during the last five years as powerful chiral Brønsted acid catalysts in many enantioselective processes. The most successful transformations carried out with chiral BINOL phosphates include C-C bond formation reactions. The recent advances have been reviewed in this article with a focus being placed on hydrocyanations, aldol-type, Mannich, Friedel-Crafts, aza-ene-type, Diels-Alder, as well as cascade and multi-component reactions.

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Year:  2010        PMID: 20820680     DOI: 10.1039/c0ob00209g

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  17 in total

1.  Origins of stereoselectivities in chiral phosphoric acid catalyzed allylborations and propargylations of aldehydes.

Authors:  Hao Wang; Pankaj Jain; Jon C Antilla; K N Houk
Journal:  J Org Chem       Date:  2013-01-18       Impact factor: 4.354

2.  Regiodivergent Glycosylations of 6-Deoxy-erythronolide B and Oleandomycin-Derived Macrolactones Enabled by Chiral Acid Catalysis.

Authors:  Jia-Hui Tay; Alonso J Argüelles; Matthew D DeMars; Paul M Zimmerman; David H Sherman; Pavel Nagorny
Journal:  J Am Chem Soc       Date:  2017-06-19       Impact factor: 15.419

3.  Enantioselective Intramolecular Allylic Substitution via Synergistic Palladium/Chiral Phosphoric Acid Catalysis: Insight into Stereoinduction through Statistical Modeling.

Authors:  Cheng-Che Tsai; Christopher Sandford; Tao Wu; Buyun Chen; Matthew S Sigman; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-30       Impact factor: 15.336

4.  Brønsted Acid/Lewis Acid Cooperatively Catalyzed Addition of Diazoester to 2H-chromene Acetals.

Authors:  Yi Luan; Yue Qi; Hongyi Gao; Qianqian Ma; Scott E Schaus
Journal:  European J Org Chem       Date:  2014-11-01

5.  Asymmetric Induction via a Helically Chiral Anion: Enantioselective Pentacarboxycyclopentadiene Brønsted Acid-Catalyzed Inverse-Electron-Demand Diels-Alder Cycloaddition of Oxocarbenium Ions.

Authors:  Chirag D Gheewala; Jennifer S Hirschi; Wai-Hang Lee; Daniel W Paley; Mathew J Vetticatt; Tristan H Lambert
Journal:  J Am Chem Soc       Date:  2018-03-06       Impact factor: 15.419

6.  Asymmetric Synthesis of β-Amino Amides by Catalytic Enantioconvergent 2-Aza-Cope Rearrangement.

Authors:  C Guy Goodman; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2015-11-12       Impact factor: 15.419

7.  Phosphothreonine as a catalytic residue in peptide-mediated asymmetric transfer hydrogenations of 8-aminoquinolines.

Authors:  Christopher R Shugrue; Scott J Miller
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-05       Impact factor: 15.336

8.  Asymmetric Synthesis of β-Substituted α-Methylenebutyro- lactones via TRIP-Catalyzed Allylation: Mechanistic Studies and Application to the Synthesis of (S)-(-)-Hydroxymatairesinol.

Authors:  Michael Fuchs; Markus Schober; Andreas Orthaber; Kurt Faber
Journal:  Adv Synth Catal       Date:  2013-08-29       Impact factor: 5.837

9.  Catalytic Asymmetric Reactions of 4-Substituted Indoles with Nitroethene: A Direct Entry to Ergot Alkaloid Structures.

Authors:  Simone Romanini; Emilio Galletti; Lorenzo Caruana; Andrea Mazzanti; Fahmi Himo; Stefano Santoro; Mariafrancesca Fochi; Luca Bernardi
Journal:  Chemistry       Date:  2015-10-21       Impact factor: 5.236

10.  Enantioselective Michael addition/iminium ion cyclization cascades of tryptamine-derived ureas.

Authors:  Isabelle Aillaud; David M Barber; Amber L Thompson; Darren J Dixon
Journal:  Org Lett       Date:  2013-05-30       Impact factor: 6.005

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